Vacation rentals in Waupun

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Top-rated vacation rentals in Waupun

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Guest favorite

The living area features a light-colored sofa paired with two armchairs, accompanied by a small table. A decorative rug adds warmth to the hardwood floor. Natural light streams in through large windows, offering views of the surrounding trees.

Cottage in Princeton

4.96 out of 5 average rating, 199 reviews

RiverFront Cottage>Private Pier>Firepit & Wildlife

Cute little cottage located right on the Fox River overlooking the peacefulness nature has to offer. Enjoy your very own private dock as well as 200 feet of river frontage surrounded by tall mature trees. Be submerged by the community of fishermen (& women) located on Puckaway Lake, surround yourself with wildlife, or paddle down the Fox River. Soak up the sun on the dock or learn how to build the best fire in the fire pit! The adventure is all around you! Which one will you be choosing?

Top guest favorite

Apartment in Watertown

4.97 out of 5 average rating, 247 reviews

The Ernest Inn - Located downtown Watertown

Welcome to the perfect "home" away from home. This apartment is located in a historical building in the heart of downtown Watertown right on Main Street. This apartment features a complete kitchen, a working typewriter, a record player, a collection of classic vinyl, wifi, a smart tv, a brand new stone tile bathroom, and a back porch to relax and take in the sounds of downtown. This apartment is perfect for just one or two but can accommodate up to 6 guests. Licensed, insured, and inspected.

Guest favorite

A spacious living area is presented with a large sectional sofa, a coffee table, and a patterned area rug. Light streams through a window, illuminating the room. A decorative plant adds a natural touch, while recessed lighting enhances the ambiance.

Home in Beaver Dam

4.91 out of 5 average rating, 69 reviews

Cute two bedroom ranch style home!

Just a 5minute walk from Beaver Dam Lake, you find a peaceful town centrally located between the Madison and the Fox Valley Areas. I’ve been remodeling my home for 2years. Neighbors surrounding me are friendly but quiet, and have pets! There are 5 parks within a 20minute walk that offer; water sport rentals on the lake, fishing, golf, basketball, baseball, and a Walmart, Piggly Wiggly, Menards, and LOTS of food within driving distance in town. I enjoy it here, hope to share it with you!

Top guest favorite

The cabin's exterior features a modern design with a dark green facade and a sloped metal roof. Large windows reflect the surrounding greenery, while a gravel pathway leads to the entrance, framed by vibrant foliage and a landscaped yard.

Cabin in Cascade

5 out of 5 average rating, 143 reviews

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

Guest favorite

Apartment in Ripon

4.95 out of 5 average rating, 57 reviews

Downtown Loft with historic charm

Stay in historic downtown Ripon, less than a block away from it all! It has large beautiful windows to watch the downtown bustle, as well as see the magical night-time lights. The moment your leave the front door you'll have famous shops, on point drinks, amazing food, Wisconsin ice cream, retro candy, coffee shop, and much more! 10 minutes from Green Lake! 30 minutes from Oshkosh and Fond du Lac. Less than 90 minutes away from Appleton, Green Bay, Madison, Milwaukee, etc.

Top guest favorite

A historic stone church converted to a residence is shown, featuring arched windows and a well-maintained exterior. The entrance is accessible via a set of steps leading to a patio area adorned with landscaping, including grass, flowers, and decorative elements.

Home in Campbellsport

4.99 out of 5 average rating, 175 reviews

Gleason's Chouse

You'll love staying in our unique home, in a quiet neighborhood. This is a recently remodeled 1867 church converted to a "Chouse". Featuring 2 bedrooms, Full Kitchen, 1 Bathroom, Balcony, Parking, and a Gazebo.. all beautifully complimented by a range of antiques and decorations. 8 Miles East of Hwy 41, a 45 min drive to Oshkosh or an hour to Milwaukee. Just down the from Lake Bernice & Eisenbahn Bike Trail. Also close enough to the Kettle Moraine Forest to hike and sightsee!

Top guest favorite

A cozy outdoor fire pit area is illuminated by soft twinkling string lights. An Adirondack chair is positioned nearby, facing the glowing fire, surrounded by landscaped stones and plants, creating an inviting atmosphere for evening gatherings.

Cabin in Fox Lake

4.96 out of 5 average rating, 190 reviews

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing, swimming and boating and in the winter have fun ice fishing on beautiful Fox Lake! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum, including children. *All dogs/pets must be pre-approved by the host. There is a $50 pet fee/stay.

Guest favorite

Three decorative lanterns are arranged on a wooden table, featuring intricate rope designs. A blue runner adds contrast to the table's natural wood. In the background, modern seating is visible, framed by large windows that bring in natural light and showcase views of the lake.

Home in Beaver Dam

4.91 out of 5 average rating, 116 reviews

LakeLife is Dam Good! 4 Bedroom Waterfront Home

Fun for the whole family at this stylish lakeside home in the heart of Beaver Dam. The house as everything a group needs and wants for the perfect weekend, week, or overnight adventure. From the open floor plan living room to the exposed game room basement that leads right out to the lakeside yard. We've filled this home with all the touches needed to guarantee lake life living. The backyard overlooks thousands of acres of lake with endless lake views.

Top guest favorite

A cozy kitchen area is presented with a wooden table at its center, featuring a vase of flowers. Surrounding the table are several stools in varying colors. The kitchen showcases stainless steel appliances and shelves filled with dishware, while photos and notes are displayed on clipboards along the wall.

Apartment in Ripon

4.97 out of 5 average rating, 239 reviews

The Hideaway Ripon WI -just 12 min to Green Lake

APARTMENT: This welcoming walk up flat is located on historic downtown Watson Street where you will find boutique shopping, and your choice of restaurants steps away! It’s walking distance to Knuth Brewery. a short 10 minute drive to Vines and Rushes winery. 12 minute drive to Green Lake. 30 minute drive to Oshkosh and Fond Du Lac. 50 minute drive to Lambeau Field in Green Bay. This renovated space will have you wanting to stay again and again.

Top guest favorite

A view of a fire pit featuring a gentle flame against a serene lake backdrop at dusk. The horizon displays soft gradients of orange and blue. Silhouettes of adirondack chairs and a boat dock can be seen in the distance, enhancing the tranquil atmosphere.

Cottage in Fond du Lac

4.99 out of 5 average rating, 287 reviews

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

Top guest favorite

A warm fire burns brightly in a stone firepit, with flames dancing and casting light against the surrounding evening darkness. The full moon is visible in the night sky above, providing a serene contrast to the flickering flames. A stone bench can be seen nearby.

Guest suite in Helenville

4.95 out of 5 average rating, 366 reviews

Chic Loft Surrounded by Nature

This charming shabby chic loft sits in the heart of the country between Madison and Milwaukee. The Lighthouse Farm is also a wedding/event venue (please inquire for more details) . A quiet relaxing environment, with lots of open space, natural sunlight and lush green landscape. Great for those looking to get away with easy access to metropolitan areas, lakes, rivers and hiking/biking trails.

Guest favorite

Cottage in Fox Lake

4.85 out of 5 average rating, 317 reviews

The Little White Cabin, Fox Lake WI

This 2 bedroom rustic cottage feels like you're home at the beach. Light colors, easy comfort. Everything you would expect for a summer cottage, boat launch is close, great fishing, water skiing, jet skiing. Winters are for ice fishing and snow mobiles. Cozy comfort. If you are a hunter, this is your cabin for longer term rentals during fall/winter. LGBTQ friendly!